Hi Kevin,
We recently implemented the automatic template upgrade without asking the end user, and in general this is working fine as it should. One thing to be aware of though, is that if the contracts in your database are based on several different templates (as it was in our case), then deactivating one of these will make an amendment to contracts that are based on the deactivated template cause an error in the system and log you out. The only fix to either 1) reactivate the old template and keep it alive until the contracts based on this template have expired, or 2) re-register the contracts to be based on your new template. We chose option no. 1 and added conditions to the template to make sure that no new contracts were registrered on that template.
The information about the assembled PDFs is new to me - I assume this only applies if you have chosen Docusign as an e-signing provider? We are considering getting an e-signing solution at some point and this fact will definately affect the choice of provider. I would be happy to hear inputs from people having challenges with the mentioned combination.